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Phosphine isocoumarin salt and preparation method thereof

A technology of isocoumarin and alkali metal salt, which is applied in the field of phosphine isocoumarin salt and its preparation, can solve the problems of limited practical application and poor water solubility, and achieve good application prospects, improved water solubility, and simple and convenient preparation method

Inactive Publication Date: 2008-03-19
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the poor water solubility of phosphonoisocoumarin ester A greatly limits the practical application of this class of compounds

Method used

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  • Phosphine isocoumarin salt and preparation method thereof
  • Phosphine isocoumarin salt and preparation method thereof
  • Phosphine isocoumarin salt and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019]

[0020] Typical operation for preparing phosphineisocoumarin alkali metal salt: under nitrogen protection, add 50mg (0.175mmol) 3-phenylphosphineisocoumarin ethyl ester, 9mg (0.210mmol) LiCl and 1ml anhydrous acetone into a 25ml egg-shaped bottle , reflux (oil bath temperature about 60° C.) and stirred for 12 hours. TLC detected that the reaction was complete. The acetone solvent was removed under reduced pressure, and the obtained white solid was washed with icy acetone. After drying, 37 mg of white solid was obtained, and the yield was 80%. Its solubility in water is about 0.080g / 1g water. 1 H NMR: δ7.74-7.83 (m, 3H), 7.22-7.34 (m, 6H), 6.82 (s, 1H); ESI-MS: 287 (M+Na, 100).

Embodiment 2

[0022]

[0023] The typical operation of preparing phosphine isocoumarin sodium salt: wherein the phosphine isocoumarin ester is 7-chloro-3-phenylphosphine isocoumarin ethyl ester, the molar amount of the reactant is the same as in Example 1, and the experimental operation is basically the same as the implementation Example 1, the difference is that the alkali metal salt used is NaI, the reaction solvent is anhydrous DMF, the reaction temperature is 80° C., and the reaction is carried out for 15 hours. After the reaction, toluene is added to azeotropically remove the DMF solvent under reduced pressure. The product was a white solid in 82% yield. Its solubility in water is about 0.085g / 1g water. 1 H NMR: δ7.74-7.80(m, 2H), 7.66-7.75(m, 1H), 7.29-7.38(m, 4H), 6.75(s, 1H); ESI-MS: 337(M+Na, 100 ).

Embodiment 3

[0025]

[0026] The typical operation of preparing phosphine isocoumarin potassium salt: wherein the phosphine isocoumarin ester used is 7-methoxy-4-bromo-3-phenylphosphine isocoumarin ethyl ester, and the molar amount of the reactant is the same as in Example 1 , the experimental operation is basically the same as in Example 2, except that the alkali metal salt used is KI, the reaction solvent is anhydrous 1,4-dioxane, the reaction temperature is 80°C, and the reaction is carried out for 12 hours. After the reaction, the reaction is removed under reduced pressure. 1,4-Dioxane solvent. The product was a white solid in 75% yield. Its solubility in water is about 0.075g / 1g water. 1 H NMR: δ7.81-7.86 (m, 1H), 7.61-7.65 (m, 2H), 7.38-7.42 (m, 3H), 7.21-7.32 (m, 2H), 3.85 (s, 3H); ESI- MS: 427 (M+Na, 100).

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Abstract

The present invention relates to a new phosphonic isocoumarin salt and a preparation method. The compound of the present invention has a molecular formula shown on the right, wherein, R = alkyl of R = H, C1-10, naphthenic base of C3-7, aryl, the substituted derivatives; Z = Li, Na, K, Rb, Cs; Y = H, alkyl of C1-4, alkoxyl, carbonyl, halogen, CN, CF3, NO2, OH, amidocyanogen, aryl; X = H, C1, Br, I, alkyl of C1-10, naphthenic base of C3-7, aryl, the substituted derivatives. The phosphonic isocoumarin salt is prepared by the reaction of phosphonic isocoumarin ester under the function of alkali metal salt. The phosphonic isocoumarin salt of the present invention has certain water solubility and can be applied to the related fields of enzyme inhibitors, anti-rumor, etc.

Description

technical field [0001] The invention relates to a phosphorus-containing heterocyclic compound, in particular to a phosphine isocoumarin salt (benzoenol phosphonolactone) and a preparation method thereof. Background technique [0002] Organophosphorus compounds not only play a very important role in life systems, but also have a wide range of commercial applications, such as insecticides, herbicides, flame retardants and lubricants, among them, many organophosphorus heterocyclic compounds with important biological activities It has been continuously discovered and synthesized (Engel, R., Ed. Handbook of Organophosphorus Chemistry; Marcel Dekker: New York, 1992; Chapter 11; Quin, L.D., Ed. A Guide to Organophosphorus Chemistry; John Wiley & Sons: New York, 2000; Chapter 11). In the previous work of the inventor, a new type of phosphorus heterocyclic compound with potential biological activity was synthesized for the first time, that is, phosphine isocoumarin ester A (patent No...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6574
Inventor 彭爱云李保健郭御卷
Owner SUN YAT SEN UNIV
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